Succinic acid

Succinic acid
IUPAC name Butanedioic acid
Other names ethane-1,2-dicarboxylic acid
Identifiers
CAS number	110-15-6 Y
PubChem	1110
ChemSpider	1078 Y
UNII	AB6MNQ6J6L Y
DrugBank	DB00139
ChEBI	CHEBI:15741 Y
ChEMBL	CHEMBL576 Y
Jmol-3D images	Image 1
SMILES C(CC(=O)O)C(=O)O
InChI InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Y Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N Y InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Key: KDYFGRWQOYBRFD-UHFFFAOYAC
Properties
Molecular formula	C4H6O4
Molar mass	118.09 g mol−1
Density	1.56 g/cm3
Melting point	184 °C, 457 K, 363 °F ()
Boiling point	235 °C, 508 K, 455 °F ()
Solubility in water	58 g/L (20 °C)
Acidity (pKa)	pKa1 = 4.2 pKa2 = 5.6
Hazards
Flash point	206 °C (403 °F)
Related compounds
Other anions	sodium succinate
Related carboxylic acids	propionic acid malonic acid butyric acid malic acid tartaric acid fumaric acid pentanoic acid glutaric acid
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Succinic acid ( /səkˈsɪnɨk/; IUPAC systematic name: butanedioic acid; historically known as spirit of amber) is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

The carboxylate anion is called succinate and esters of succinic acid are called alkyl succinates.

At room temperature, pure succinic acid is a solid that forms colorless, odorless crystals. It has a melting point of 185 °C and a boiling point of 235 °C. It is a diprotic acid.

History

Spirit of amber was originally procured from amber by pulverising and distilling it using a sand bath. It was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.

Succinic acid is now used within the food and beverage industry, primarily as a sweetener. Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.

Biochemical role

Succinate is a component of the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:

succinate + FAD → fumarate + FADH₂.

This is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC). The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three Fe₂S₂ clusters part of subunit B.

Succinic acid can be converted into fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation.

Fermentation

See also: Acids in wine

Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

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Citric_acid_cycle edit

Safety

The acid is combustible and corrosive, capable of causing burns.

In nutraceutical form as a food additive and dietary supplement, is safe and approved by the U.S. Food and Drug Administration. As an excipient in pharmaceutical products it is used to control acidity and, more rarely, in effervescent tablets.

See also

• Oil of amber, procured by heating succinic acid.

References

•  This article incorporates content from the 1728 Cyclopaedia, a publication in the public domain.

External links

• MSDS Data
• FDA
• Succinic Acid
• Calculator: Water and solute activities in aqueous succinic acid